PCT Application Publication No. WO98/27055 discloses indanylamine and aminotetralin compounds, such as those of Formula I below, which are useful to treat dementias, depression, Attention Deficit Disorder (ADD), Attention Deficit and Hyperactivity Disorder (ADHD), Tourette's Syndrome, Alzheimer's Disease and other disorders. The indanylamine derivatives disclosed have been shown to have biological effects in animal models of neurological disease. In addition, PCT Application Publication No. WO98/27055 discloses methods for preparation of such compounds.
wherein b is 1 or 2; m is 0-3; Y is O or S; X is halo; R1 is hydrogen or C1-4 alkyl; R2 is hydrogen, C1-4 alkyl, or optionally substituted propargyl; and R3 and R4 are each independently hydrogen, C1-8 alkyl, C6-12 aryl, C6-12 aralkyl, each optionally halo substituted.
R(+)-6-(N-methyl,N-ethyl-carbamoyloxy)-N′-propargyl-1-aminoindan, also known as (3R)-3-(prop-2-ynylamino)-2,3,-dihydro-1H-inden-5-yl ethylmethylcarbamate, and carbamic acid, ethylmethyl-, (3R)-2,3-dihydro-3-(2-propynylamino)-1H-inden-5-yl ester, is disclosed in PCT Application Publication No. WO98/27055, specifically compound 76 in Table 5. In addition, salts are disclosed, including the ½ L-tartrate salt. This salt has been given the nonproprietary name ladostigil tartrate. Its CAS registry number is 209394-46-7.
PCT Application Publication No. WO98/27055 describes laboratory scale preparations of its compounds. Thus, PCT Application Publication No. WO98/27055 does not disclose whether and how any of the compounds can be prepared on a larger scale, such as in a pilot plant and production plant.